Novel episulfide compounds and their optical material compositions

Abstract

The present invention relates to a novel organic material field. The episulfide compound having a sulfoxide structure can effectively improve the alkali corrosion resistance of optical material substrates due to the presence of polar groups, thereby increasing the yield of substrates and reducing production costs.

Description

Technical Field

[0001] The present invention belongs to the field of novel organic materials and optical materials, and relates to optical materials suitable for use in plastic lenses, prisms, optical fibers, information storage substrates, filters, etc., more specifically, novel episulfide compounds and optical material compositions thereof.

Background Art

[0002] In recent years, with the development of optical resin technology, continuously increasing the refractive index of optical resin lenses has become the goal of future lenses. As raw materials for ultra-high refractive index resin lenses, sulfur-containing compounds, particularly polycyclic sulfur compounds and their blending technologies, have been developed. In the manufacturing process of optical resin lenses, after primary curing is completed, demolding and mold opening are performed, and edge processing and cleaning of the obtained substrate are carried out. The purpose of cleaning is to remove unreacted monomers and pulverized solid powders. In order to ensure the cleaning effect, it is necessary to use a solution with a certain alkali concentration and control the cleaning temperature. During the cleaning process, the resin lens may be corroded or burned due to the influence of alkali concentration and temperature, resulting in a decrease in the yield of the substrate and an increase in manufacturing cost. In the prior art, there is no technical solution to solve this problem.

[0003] Therefore, providing an optical material with more excellent performance and alkali corrosion resistance has become one of the urgent issues in this field.

Summary of the Invention

Problems to be Solved by the Invention

[0004] To fill a gap in existing technologies, the present invention provides novel episulfide compounds and optical material compositions thereof. The episulfide compounds have a sulfoxide structure, and the presence of this polar group effectively improves the alkali corrosion resistance of optical material substrates, reduces the burning rate of the substrates, thereby improving substrate yield and reducing manufacturing costs. Its structure is the same bifunctional episulfide structure as bis(β-epithiopropyl) sulfide, and the sulfur content does not change significantly, so it does not affect other performance indicators such as the refractive index of the product. [Means for solving the problem]

[0005] The specific technical solution of this application is as follows: First, the inventors provide an episulfide compound represented by formula (1).

[0006] [ka]

[0007] The following methods are possible, but are not limited to, the preparation of the episulfide compound represented by formula (1) above. One method involves reacting an epoxy compound represented by formula (3) with a sulfidating reagent such as thiourea or thiocyanate under acidic conditions.

[0008] [ka]

[0009] Preferably, the sulfiding reagent is selected from one or more of thiourea, potassium thiocyanate, ammonium thiocyanate, and sodium thiocyanate, with thiourea being preferred. The molar ratio of the amount of sulfiding reagent to the epoxy functional group in formula (3) is 1.0 to 3.0, preferably 2.0 to 2.5. A molar ratio of less than 2.0 results in a low raw material conversion rate, and a molar ratio greater than 2.5 results in a low selectivity for the product represented by formula (1), so both are undesirable.

[0010] Acids used in the reaction process include nitric acid, hydrochloric acid, sulfuric acid, boric acid, arsenic acid, arsenous acid, pyroaric acid, phosphoric acid, phosphorous acid, hypophosphorous acid, hydrocyanic acid, chromic acid, other inorganic acids, formic acid, acetic acid, peroxyacetic acid, thioacetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, valeric acid, hexanoic acid, octanoic acid, naphthenic acid, methyl mercaptopropionic acid, malonic acid, glutaric acid, adipic acid, cyclohexanecarboxylic acid, thiodipropionic acid, dithiodipropionic acid, maleic acid, benzoic acid, phenylacetic acid, o-toluic acid, m- Organic carboxylic acids such as toluic acid, p-toluic acid, salicylic acid, 2-methoxybenzoic acid, 3-methoxybenzoic acid, benzoylbenzoic acid, phthalic acid, isophthalic acid, terephthalic acid, diphenylglycolic acid, naphthoic acid, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic anhydride, phthalic anhydride, pyromellitic anhydride, trimellitic anhydride, trifluoroacetic anhydride, mono-, di-, and trimethyl phosphates, mono-, di-, and triethyl phosphates, mono-, di-, and triisobutyl phosphates, phosphoric acid Phosphate esters such as mono, di, and trilauryl, and phosphite esters consisting of phosphates and phosphates, organophosphorus compounds such as dialkyldithiophosphates represented by dimethyldithiophosphate, phenol, catechol, tert-butylcatechol, 2,6-di-tert-butyl-p-cresol, 2,6-di-tert-butylethylphenol, resorcinol, hydroquinone, phloroglucinol, pyrogallol, p-cresol, ethylphenol, butylphenol, nonylphenol, hydroxyphenylacetic acid, hydroxyphenylpropionic acid, hydroxyphenylacetamide, methyl hydroxyphenylacetate, hydroxyphenylethyl acetate, p-hydroxyphenylethanol, p-hydroxyphenylethylamine, hydroxybenzaldehyde, phenylphenol, bisphenol A, 2,2'-methylene-bis(4-methyl-6-tert-butylphenol), bisphenol-F, bisphenol-S, α-naphthol, β-naphthol, aminophenol, chlorophenol, 2,4,Phenols such as 6-trichlorophenol, methanesulfonic acid, ethanesulfonic acid, butanesulfonic acid, dodecanesulfonic acid, benzenesulfonic acid, o-toluenesulfonic acid, m-toluenesulfonic acid, p-toluenesulfonic acid, ethylbenzenesulfonic acid, butylbenzenesulfonic acid, dodecylbenzenesulfonic acid, p-phenolsulfonic acid, o-cresolsulfonic acid, aminobenzenesulfonic acid, p-aminobenzenesulfonic acid, 4B-acids, 2,2'-diaminestilbenesulfonic acid, biphenylsulfonic acid, α-naphthalenesulfonic acid, β-naphthalenesulfonic acid, peracids, lorentzic acid, phenylJ acid, and other sulfonic acids. Acids may be used individually or in mixtures of two or more. Preferably, organic carboxylic acids such as formic acid, acetic acid, peroxyacetic acid, thioacetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, valeric acid, hexanoic acid, octanoic acid, naphthenic acid, methyl mercaptopropionic acid, malonic acid, glutaric acid, adipic acid, cyclohexanecarboxylic acid, thiodipropionic acid, dithiodipropionic acid, maleic acid, benzoic acid, phenylacetic acid, o-toluic acid, m-toluic acid, p-toluic acid, salicylic acid, 2-methoxybenzoic acid, 3-methoxybenzoic acid, benzoylbenzoic acid, phthalic acid, isophthalic acid, terephthalic acid, diphenylglycolic acid, α-naphthoic acid, β-naphthoic acid, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic acid anhydride, phthalic anhydride, pyromellitic anhydride, trimellitic anhydride, trifluoroacetic anhydride, etc.

[0011] More preferred are formic acid, acetic acid, peracetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, valeric acid, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic anhydride, phthalic anhydride, pyromellitic anhydride, trimellitic anhydride, and trifluoroacetic acid. Acetic acid is the most preferred.

[0012] The molar ratio of acid to epoxy functional group in formula (3) is 0.001 to 1.0, with a more preferable molar ratio being 0.01 to 0.5. A molar ratio of less than 0.01 results in a low raw material conversion rate, and a molar ratio greater than 0.5 results in a low selectivity for the episulfide compound represented by formula (1), so both are undesirable.

[0013] In the above manufacturing method, it is preferable to use a solvent. Examples of reaction solvents include alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran, dioxane and other ethers, hydroxy ethers such as methyl cellosolve, ethyl cellosolve, and butyl cellosolve, aromatic hydrocarbons such as benzene and toluene, dichloromethane, chloroform, chlorobenzene and other halogenated hydrocarbons, and water. Preferably, one or two mixed solvents selected from the group consisting of methanol, isopropyl alcohol, toluene, and methylene chloride are used. There are no special requirements for the volume of the solvent as long as it can completely dissolve the sulfiding reagent.

[0014] The reaction temperature is typically 10-60°C, preferably 25-40°C. Below 10°C, the sulfidation reagent has poor solubility, and above 60°C, polymers are formed and side reactions increase.

[0015] After obtaining the episulfide compound described above, the present invention further provides an optical material composition containing a polymer compound mainly composed of a compound represented by formula (1) and a compound represented by formula (2). The compound represented by formula (1) accounts for 0.001 to 6.0% of the total weight of the optical material composition, and more preferably the compound represented by formula (2) accounts for 0.1 to 3%.

[0016] [ka]

[0017] If the content of the compound of formula (1) is less than 0.001%, alkali resistance is poor, and if it exceeds 6.0%, it affects the impact resistance of the optical material, making subsequent processing and use unfavorable. Furthermore, when the compound represented by formula (2) is used as the polymerizable compound, the proportion of the compound represented by formula (2) in the optical material composition of the present invention is 50 to 99.999% of the total weight of the optical material composition, and more preferably 70 to 99%.

[0018] The polymerizable compounds described herein may be present together with thiol compounds and isocyanate compounds, in addition to the compound represented by formula (2).

[0019] When the total weight of the optical material composition is taken as 100%, the content of the thiol compound is usually 1 to 20%, preferably 3 to 15%, and can improve the heat resistance of the optical material. If the content of the thiol compound is 1% or more, yellowing during lens molding can be suppressed, and if it is 20% or less, a decrease in heat resistance can be prevented. The thiol compounds used in the present invention may be used individually or as a mixture of two or more types.

[0020] Specific candidate thiol compounds include 2-mercaptoethanol, 3-mercaptopropanol, 2-hydroxypropyl mercaptan, n-hexyl mercaptan, n-octyl mercaptan, bis(2-mercaptoethyl) sulfide, 2,5-dimercaptomethyl-1,4-dithiane, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiooctane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithioundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithioundecane, and 5,7- The substance is one or more of the following: dimercaptomethyl-1,11-dimercapto-3,6,9-trithioundecane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, pentaerythritol tetramercaptopropionate, pentaerythritol tetrakis(mercaptoacetate), trimethylolpropane tris(thioglycolate), trimethylolpropane trimercaptopropionate, preferably one or more of 2-mercaptoethanol, 3-mercaptopropanol, 2-hydroxypropyl mercaptan, bis(2-mercaptoethyl)sulfide, and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiooctane.

[0021] The isocyanate compound content is typically 1-20%, preferably 3-15%, of the total weight of the optical material composition, with the total weight being 100%. A content of 1% or more of the isocyanate compound can improve the strength of the optical material, while a content of 20% or less can suppress the deterioration of color tone. The isocyanate compounds used in this invention may be used individually or in mixtures of two or more types.

[0022] Preferably, the isocyanate compound contains at least two isocyanate groups, and the isocyanate compound is diethyl diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, cyclohexane diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate, 2,6-bis(isocyanatomethyl)decalin, tolylene diisocyanate, o-toluidine diisocyanate, diphenylmethane diisocyanate, diphenyl ether diisocyanate, 2,2'-bis(4-isocyanatophenyl)propane, triphenylmethane triisocyanate, bis(diisocyanatotolyl)phenylmethane, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 4,4'-diisocyanate biphenyl, dicyclohexylmethane-4,4'-diisocyanate, 1,1'-methylenebis(4-isocyanatobenzene), m-xylylene diisocyanate, p-xylylene diisocyanate, m-tetramethylxylylene diisocyanate, p-tetramethylxylylene diisocyanate, bis(isocyanatomethyl)norbornene, bis(isocyanatomethyl)adamantane, thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate. Preferably, it is selected from isophorone diisocyanate, m-xylylene diisocyanate, and 1,3-bis(isocyanatomethyl)cyclohexane.

[0023] Adding the thiol compound and the isocyanate compound to a polymer compound mainly composed of the compounds represented by the general formula (1) and the general formula (2) does not affect the alkali corrosion resistance of the final material.

[0024] Based on the above composition for optical materials, the present inventors provide a polymerization curable composition containing any one of the combinations of the above compositions for optical materials and a polymerization catalyst in an amount of 0.01% to 1% based on the total weight of the composition for optical materials. As the polymerization catalyst, imidazoles and phosphines can be used, and more preferably tetrabutylphosphonium bromide can be used as the polymerization catalyst.

[0025] The addition amount of the polymerization catalyst varies depending on the components of the composition, the mixing ratio, and the polymerization curing method, and cannot be generally stated. However, 0.03% to 0.5% is preferable based on the total weight of the composition for optical materials. If the addition amount of the polymerization catalyst exceeds 1%, rapid polymerization may occur. If the addition amount of the polymerization catalyst is less than 0.01%, the curing of the composition for optical materials may be insufficient and the heat resistance may decrease.

[0026] Also, when manufacturing the corresponding optical material, the practicality of the obtained optical material can be further improved by adding additives to the above polymerization curable composition. That is, the polymerization curable composition of the present invention may contain additives such as an ultraviolet absorber, a release agent, a blue agent, and a red agent. The ultraviolet absorber is a benzotriazole compound, particularly preferably 2-(2-hydroxy-tert-octylphenyl)-2H-benzotriazole (UV-329), and the addition amount is 0.001% to 1% of the total weight of the polymerization curable composition, and more preferably 0.01% to 0.5%. The blue agent and the red agent are added according to the needs of the actual optical material, and there is no particular regulation regarding the addition amount. The release agent is one or more selected from di-n-butyl phosphate, El310, nonylphenol polyoxyethylene ether phosphate, and Zelec® UN, and the addition amount is 0.001% to 1% of the total weight of the polymerization curable composition, more preferably 0.01% to 0.5%.

[0027] The present invention also provides an optical material obtained by curing the above polymerizable composition. The specific steps are as follows: a) The optical material composition is uniformly mixed to obtain a mixed reaction product; b) The reaction mixture obtained in step a) is poured into a mold through a filter film to perform primary curing; after demolding, edge grinding and multi-tank ultrasonic cleaning are continued, and after cleaning is completed, secondary curing is performed to obtain an optical resin material.

[0028] In this process, the heating program for the first curing described in step b) involves maintaining an initial temperature of 15-25°C for 2.0-3.5 hours, then heating for 10-15 hours to raise the temperature to 45-60°C, then overheating for 2.0-4.0 hours to raise the temperature to 75-90°C, and finally cooling for 1.5-2.5 hours to 60-75°C. The temperature for the second curing in step b) is 80-110°C, and the time is 2-4 hours.

[0029] The process parameters for multi-tank ultrasonic cleaning are as follows:

[0030] [Table 1]

[0031] The specific cleaning process and reagents used can be found in the methods and reagents documented in the existing patent CN104802430B. The optical material obtained above can be used in the fabrication of optical lenses.

[0032] In summary, compared to prior art, the episulfide compound obtained in this application incorporates a sulfoxide structure, and the presence of this polar group effectively improves the alkali corrosion resistance of optical material substrates, reduces substrate burning due to impurity points caused by corrosion, thereby improving substrate yield and reducing manufacturing costs. [Brief explanation of the drawing]

[0033] [Figure 1] This is the mass spectrum of the novel episulfide compound in Example 1. [Figure 2] This is the 1H NMR spectrum of the novel episulfide compound from Example 1. [Figure 3] Figures 2 and 3 show the 13C NMR spectra of the novel episulfide compound from Example 1. 1H NMR (CDCl3) δ=2.21 ppm (1H), δ=2.32 ppm (2H), δ=3.02 ppm (2H); 13C NMR (CDCl3) δ=24.8 ppm, 28.6 ppm, 63.7 ppm. [Modes for carrying out the invention]

[0034] The above-mentioned content of the present invention will be described in detail below in the form of examples, but this does not mean that the scope of the subject matter of the present invention is limited to the following examples. All techniques implemented based on the above-mentioned content of the present invention fall within the scope of the present invention, and unless otherwise specified, all raw materials used in the following examples are commercially available products.

[0035] To further illustrate the present invention, the following embodiments will be described in detail. 1) Burnt fragment rate: Burnt fragments refer to the phenomenon in which spots of impurities appear near the center of the substrate during the substrate cleaning process due to the influence of alkali concentration and temperature. In the embodiments of the present invention, 100 ultrasonically cleaned substrates were visually inspected to identify substrates with burnt fragments, and the burnt fragment rate was calculated.

[0036] 2) Yield: Product A has no impurity spots within a central radius of 3 cm. Product B has no impurity spots within a central radius of 1.5 cm, but has impurity spots between 1.5 and 3 cm. Product C contains leaf-like impurities within a central radius of 1.5 cm. Of these, products A and B are acceptable, while product C is unacceptable. In the embodiment of the present invention, 100 ultrasonically cleaned substrates were visually inspected to check for impurity spots within different central radii, and the yield was calculated.

[0037] (Example 1) Method for producing an episulfide compound represented by formula (1):

[0038] [ka]

[0039] 81 g (0.5 mol) of the compound represented by formula (3) above, 500 mL of methanol, 500 mL of toluene, 87.4 g (1.15 mol) of thiourea, and 6 g (0.1 mol) of acetic acid were added and the mixture was reacted at 30°C for 12 hours. By separating and purifying this crude product using a silica gel column by conventional methods, 48.5 g (0.25 mol) of the episulfide compound represented by formula (1) above was obtained.

[0040] [ka]

[0041] The episulfide compound represented by equation (1) was characterized by mass spectrometry and nuclear magnetic resonance spectroscopy. The results are shown in Figure 1-3. Mass spectrum (ESI): [M+H] + = 194.9972.

[0042] (Example 2) 88.4 g of bis(β-epithiopropyl) sulfide, 0.1 g of an episulfide compound represented by formula (1), 5.1 g of isophorone diisocyanate, 6.3 g of mercaptoethanol, 0.1 g of tetrabutylphosphonium bromide, 0.3 g of 2-(2-hydroxy-tert-octylphenyl)-2H-benzotriazole (UV-329), and 0.2 g of di-n-butyl phosphate are mixed and stirred for 50 minutes to obtain a prepolymer liquid. The density ρ before solidification is measured using a liquid densimeter. After vacuum degassing the prepolymer liquid for 30 minutes, it is filtered through a polytetrafluoroethylene filter membrane with a pore size of 3 μm and poured into a glass mold. Next, this mold is placed in a programmed temperature curing oven for primary curing to obtain a primary cured resin lens. The heating program for primary curing is as follows: The initial temperature was 20°C, and after holding for 2 hours, the temperature was raised to 45°C for 3.5 hours, then to 55°C for 3 hours, then to 100°C for 6 hours, and held for 4 hours. After that, the temperature was lowered over 2 hours to 70°C. The obtained primary cured resin lens substrate was demolded, multi-chamber ultrasonic cleaning was performed, and then the burnt fragment rate and yield were calculated by visual inspection. The process parameters for multi-chamber ultrasonic cleaning are as follows.

[0043] [Table 2]

[0044] The specific washing process and reagents used can be found in the methods and reagents documented in the existing patent CN104802430B, where the alkali concentration is 3% or 6%.

[0045] (Example 3) The difference from Example 2 is that 87.5 g of bis(β-epithiopropyl) sulfide and 1.0 g of the episulfide compound represented by formula (1) were added, while the other amounts of additives and the steps were the same as in Example 2.

[0046] (Example 4) The difference from Example 2 is that 86.5 g of bis(β-epithiopropyl) sulfide and 2.0 g of the episulfide compound represented by formula (1) were added, while the other amounts of additives and the steps were the same as in Example 2.

[0047] (Example 5) The difference from Example 2 is that 85.5 g of bis(β-epithiopropyl) sulfide and 3.0 g of the episulfide compound represented by formula (1) were added, while the other amounts of additives and the steps were the same as in Example 2.

[0048] (Example 6) The difference from Example 2 is that 88.4 g of bis(β-epithiopropyl) sulfide and 0.1 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration of the multi-tank ultrasonic cleaning was set to 6%. The other additive amounts and steps were the same as in Example 2.

[0049] (Example 7) The difference from Example 2 is that 87.5 g of bis(β-epithiopropyl) sulfide and 1.0 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration of the multi-tank ultrasonic cleaning was set to 6%. The other additive amounts and steps were the same as in Example 2.

[0050] (Example 8) The difference from Example 2 is that 86.5 g of bis(β-epithiopropyl) sulfide and 2.0 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration of the multi-tank ultrasonic cleaning was set to 6%. The other additive amounts and steps were the same as in Example 2.

[0051] (Example 9) The difference from Example 2 is that 85.5 g of bis(β-epithiopropyl) sulfide and 3.0 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration of the multi-tank ultrasonic cleaning was set to 6%. The other additive amounts and steps were the same as in Example 2.

[0052] (Comparative Example 1) The difference from Example 2 is that 88.5 g of bis(β-epithiopropyl) sulfide and 0 g of the episulfide compound represented by formula (1) were added, while the other amounts of additives and the steps were the same as in Example 2.

[0053] (Comparative Example 2) The difference from Example 2 is that 84.5 g of bis(β-epithiopropyl) sulfide and 4 g of the episulfide compound represented by formula (1) were added, while the other amounts of additives and the steps were the same as in Example 2.

[0054] (Comparative Example 3) The difference from Example 2 is that 82.5 g of bis(β-epithiopropyl) sulfide and 6 g of the episulfide compound represented by formula (1) were added, while the other amounts of additives and the steps were the same as in Example 2.

[0055] (Comparative Example 4) The difference from Example 2 is that 88.5 g of bis(β-epithiopropyl) sulfide and 0 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, multi-tank ultrasonic cleaning with alkali was performed. The concentration was set to 6%. The other additive amounts and steps were the same as in Example 2.

[0056] (Comparative Example 5) The difference from Example 2 is that 84.5 g of bis(β-epithiopropyl) sulfide and 4 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration of the multi-tank ultrasonic cleaning was set to 6%. Other additive amounts and steps were the same as in Example 2.

[0057] (Comparative Example 6) The difference from Example 2 is that 82.5 g of bis(β-epithiopropyl) sulfide and 6 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration of the multi-tank ultrasonic cleaning was set to 6%. The other additive amounts and steps were the same as in Example 2.

[0058] The substrate burnt-off rate and yield were calculated using the examples and comparative examples. The specific results are shown in the table below.

[0059] [Table 3]

[0060] In the table, BEPSO is an episulfide compound represented by formula (1). From the results in the table above, when the amount of episulfide compound represented by formula (1) added is 0.1 to 3.0% by mass, the sintering rate of the optical resin material lens is approximately 10%, the substrate yield is >95%, and the stability is at its highest. When the amount of episulfide compound represented by formula (1) added exceeds 3%, the sintering rate and yield do not change significantly. When the amount added is 0, the sintering rate exceeds 20%, the yield is less than 90%, and the cost increases.

[0061] Those skilled in the art can implement or use the present invention through the embodiments described above. Various modifications to these embodiments will be apparent to those skilled in the art. The general principles defined herein can be implemented in other embodiments without departing from the spirit or scope of the invention. Accordingly, the present invention is not intended to be limited to the embodiments shown herein, but rather should be given the broadest scope consistent with the principles and novel features disclosed herein.

Claims

1. A novel episulfide compound characterized by being a compound represented by the chemical formula (1). 【Chemistry 1】

2. A polymerizable compound mainly composed of the compound represented by formula (1) and the compound represented by formula (2) as described in claim 1, 【Chemistry 2】 Herein, the optical material composition is characterized in that the compound represented by formula (1) accounts for 0.001 to 6.0% of the total weight of the composition.

3. Furthermore, it contains thiol compounds and isocyanate compounds, The optical material composition according to claim 2, characterized in that the compound represented by formula (1) accounts for 0.1 to 3.0% of the total weight of the composition.

4. The optical material composition according to claim 2 or 3, characterized in that the compound represented by formula (2) accounts for 50.0 to 99.999% of the total weight of the composition.

5. The optical material composition according to claim 4, characterized in that the compound represented by formula (2) accounts for 70.0 to 99.999% of the total weight of the optical material composition.

6. A polymerizable and curable composition characterized by containing the optical material composition described in claim 2 and a polymerization catalyst in an amount of 0.01 to 1% relative to the total weight of the optical material composition.

7. The polymerization-curable composition according to claim 6, characterized in that the polymerization catalyst is imidazole or phosphine, and the amount added is 0.03% to 0.5% of the total weight of the optical material composition.

8. An optical material characterized by being obtained by curing the polymerization-curable composition described in claim 6 or 7.

9. An optical lens characterized by being manufactured using the optical material described in claim 8.

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